The Big Party

FROM JULY 2009: After launching the Playboy empire here in the 1950s, Hugh Hefner turned Chicago into a frontline of the sexual revolution, acting out his sybaritic fantasy life behind the walls of his mansion on North State Parkway. But as the freewheeling sixties gave way to the decadent seventies, things changed drastically for Hefner and the Gold Coast mansion he called home

By Bryan Smith

Published July 13, 2009

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At the hop: Hefner and friends huddle at the Playboy Mansion in 1966. Photo Gallery »

She is beautiful still in the spring sunlight, the form, the façade, the long, lovely lines. Not young, but quite fashionable, striking the same winsome pose she held when her presence along this glittering Gold Coast stretch could stop men in their tracks. They would stand before her bewitched then, desperate for her favor. Depending on who they were, it would be granted—though not always. She could be fickle that way. But such was her power, her mystery, that she never wanted for suitors.

That was long ago. The men no longer stare. They pass now with barely a glance. These days, the four-story brick and limestone Victorian-style manor house is just a building.

But for one gilded period some 40-odd years ago, 1340 North State Parkway was much more. In the abstract, it was both the epicenter of a new sexual freedom and an object of scorn; more concretely, it was the setting for some of the most notorious, celebrity-filled parties of its time. Where else might you see Frank Sinatra chuckling at a gorgeous naked woman diving into an indoor pool filled with other gorgeous naked women? Meet Joe DiMaggio and Dean Martin and Warren Beatty and the Rolling Stones in the same ballroom? Slide down a fireman’s pole to an underwater bar lit by the sparkling green of an aquarium window through which yet more gorgeous women could be seen cavorting like so many mermaids?

The building, of course, was the Playboy Mansion—the original Playboy Mansion—at a time when its owner, a West Side boy named Hugh Marston Hefner, ruled the city, if not the world.

Back then, the Playboy imprimatur festooned Chicago and environs—lines stretched outside the Playboy Club on Walton Street; the word “Playboy” blazed atop the Palmolive Building in nine-foot-high letters. Chicago was home to the Playboy Towers Hotel and the Playboy Theater, and the 1,000-acre, 300-room Playboy resort aroused sleepy Lake Geneva. It was an era when Playboy Bunnies bicycled to Schwartz’s on Rush to pick out merry widow corsets; when Playmate centerfolds struck seductive poses in studios on the Magnificent Mile; when the TV show Playboy’s Penthouse hepped it up with jazz greats in a Loop studio.

It’s been so long since Hefner lived in the Chicago mansion that these days it’s hard to believe the place existed, much less that it still stands. And, yet, there it is, beautiful on a sunny spring day, an old flame, an apparition, a silent witness to a strange, singular era in a town she loved and lost.

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During the 1960s, life inside the Playboy Mansion was a decade-long frolic Photo Gallery »

Hefner is back there, in his mind’s eye, the day I meet him at his current home—Playboy Mansion West, near Beverly Hills. He sits on a plum-striped couch in the library, a dim parlor that features a bare-breasted ceramic bust of Barbi Benton, one of Hefner’s enduring loves and the woman partly responsible for his leaving Chicago for good in 1975.

He is 83 now, his hair thinned and woven with white. He is hard of hearing in the right ear, so I am asked to sit to his left. He wears his trademark crimson smoking jacket draped, as always, over silk pajamas, which today are black. He discarded his pipe many years ago, on his doctor’s advice, after a mild stroke in 1985. But that missing piece of stagecraft, deployed in the fifties to make himself look sophisticated, hasn’t diminished the image, the bearing, the great natural charisma, the reality of who he is. He is talking about the L.A. mansion, telling me, as he does all interviewers, that it is his spiritual home. Moving here, he explains, was the best thing he’s ever done.

Still, as he speaks, his voice conveys wistfulness, and he concedes that he looks back to those years in Chicago fondly. Seeing him so at ease in the lap of his current luxury, it’s hard to imagine he would long for the grit of the Windy City, particularly given the painful chain of events that sealed his desire to leave. But so powerful were those days, those memories, that the King of Fantasy, in this late afternoon of his life, admits he would love to turn back the clock, if only for a moment. “What I would love to do,” he says, his voice taking on a curious poignancy, “would be to get in a time machine and simply walk back into that mansion in 1965.”